During the inhibition of glycopeptide transpeptidase, a serine from the enzyme reacts with the amide carbonyl of the lactam ring in penicillin antibiotic to form an enzyme - penicillin complex which inactivates the enzyme. The conversion of an amide to an an ester is not normally observed in reactions of carboxylic acid derivatives. Provide an explanation as to why the amide of a penicillin antibiotic can react with the serine of glyopeptide transpeptidase in this unexpected way. The structure of amoxicillin, a penicillin antibiotic, is shown below: HO N. OH H2N amoxicillin ... I

During the inhibition of glycopeptide transpeptidase, a serine from the enzyme reacts with the amide carbonyl of the lactam ring in penicillin antibiotic to form an enzyme - penicillin complex which inactivates the enzyme. The conversion of an amide to an an ester is not normally observed in reactions of carboxylic acid derivatives. Provide an explanation as to why the amide of a penicillin antibiotic can react with the serine of glyopeptide transpeptidase in this unexpected way. The structure of amoxicillin, a penicillin antibiotic, is shown below: HO N. OH H2N amoxicillin ... I

Biochemistry

9th Edition

ISBN:9781319114671

Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Chapter1: Biochemistry: An Evolving Science

Section: Chapter Questions

Problem 1P

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